1,3-Dibenzyl-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

Abstract

The mol­ecule of the title compound, C29H20N2O3, contains four fused rings, three are six-membered rings and one is the five-membered imidazole ring. The fused-ring system is linked to two benzyl groups. The four fused rings are folded around the O=C⋯C=O direction of the anthraquinone, with a dihedral angle of 16.36 (8)° between the two terminal rings (A and D). The imidazole ring (D) is almost perpendicular to the two benzyl groups (E and F) with dihedral angles of 86.69 (17) and 83.15 (13)°, respectively. In the crystal, adjacent mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonding.

1,3-Bis(prop-2-yn-1-yl)-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

“…For background to the pharmacological activity and potential applications of anthraquinones, see: Alves et al (2004); Ellis et al (2003); Boseggia et al (2004); Mariappan & Basa (2011); Kadarkaraisamy et al (2008). For similar compounds, see: Afrakssou et al (2010Afrakssou et al ( , 2011; Guimarã es et al (2009).…”

“…So we are interested in the synthesis of new derivatives of anthra [1,2-d]imidazole-2,6, 11-trione and their biological activities (Afrakssou et al, 2010;Afrakssou et al, (2011); Guimarães et al, 2009). The reactivity of propargyl bromide towards 1H-anthra [2, 1 -d] imidazole-2, 6, 11(3H)-trione under phase-transfer catalysis conditions using tetra n-butyl ammonium bromide (TBAB) as catalyst and potassium carbonate as base, leads to the formation of title compound in good yields (Scheme 1).…”

1,3-Bis(naphthalen-2-ylmethyl)-1H-anthra[1,2-d]imidazole-2,6,11(3H)-trione

“…when the compound is reacted with an alkyl halide in a reaction catalyzed by tetra-n-butylammonium bromide; the dibenzyl substituted derivative is synthesized in such a synthesis in high yield. The study (Afrakssou et al, 2011) is now extended to the title naphthylmethyl analog (Scheme I, Fig. 1).…”